There were 320 households out of which 29.7% had children under the age of 18 living with them, 58.1% were married couples living together, 7.8% had a female householder with no husband present, and 30.0% were non-families. 26.3% of all households were made up of individuals and 8.4% had someone living alone who was 65 years of age or older. The average household size was 2.34 and the average family size was 2.82.
In the village the population was spread out with 24.3% under the age of 18, 4.5% from 18 to 24, 24.4% from 25 to 44, 31.4% from 45 to 64, and 15.4% who were 65 years of age or older. The median age was 43 years. For every 100 females there were 98.1 males. For every 100 females age 18 and over, there were 96.2 males.
The median income for a household in the village was $40,795, and the median income for a family was $52,292. Males had a median income of $40,750 versus $27,083 for females. The per capita income for the village was $21,301. About 8.7% of families and 9.9% of the population were below the poverty line, including 14.0% of those under age 18 and 5.2% of those age 65 or over.
By the end of 1898, the line had been extended as far as Toboggan Canyon, and construction was started on a pavilion at the summit, which would provide accommodations for the anticipated tourists, once the line was completed. It consisted of a dining room, kitchen, parlor, entertainment hall, and 40 tents, set on wooden platforms. In June of 1899, The Pavilion was formally opened by John Arthur Eddy. The first visitors rode the train as far as Toboggan and finished the trip by stagecoach. Subsequently, glowing reports in area newspapers made Cloudcroft a popular destination. An additional resort, The Lodge, was built in 1899 as a more upscale alternative to The Pavilion. The railroad line arrived in Cloudcroft proper in early 1900 and in June 1900 the train depot was finished, located about west of The Pavilion. The building was occupied in June 1900. Meeting the train became a daily festivity in the village. At this point, three trains a day arrived in Cloudcroft, hauling lumber, mail, and passengers.
In 1909, The Lodge burned down and was rebuilt at its present location in 1911. The Pavilion also burned down on two separate occasions in the 1920s, but was rebuilt each time to conform with the original plans.
The Lodge had several famous guests: Judy Garland, Gilbert Roland, Clark Gable, and Pancho Villa. In the 1930s the resort was managed by Conrad Hilton, who was born and raised in San Antonio, New Mexico. According to reports, Hilton was familiar with The Lodge and wanted to be closer to his family, while his own hotel chain slowly began its climb to prominence.
As automobiles grew in use, the train line began losing money. The last passenger train was in 1938, and the last freight train was in 1947. Since then, tourism in Cloudcroft has grown beyond The Lodge and Pavilion and into Burro Street near Highway 82 where many small shops and restaurants have sprung and summer street dances are hosted. The local population has not grown exceedingly in the past decades, sitting between 700-800 residents.